Trimethylsulfoxonium iodide

Base Information

• Chemical Name: Trimethylsulfoxonium iodide
• CAS No.: 1774-47-6
• Deprecated CAS: 76570-08-6,305859-81-8,1646683-13-7
• Molecular Formula: C3H9IOS
• Molecular Weight: 220.074
• Hs Code.: 29309070
• European Community (EC) Number: 217-204-2
• NSC Number: 71213
• DSSTox Substance ID: DTXSID001014581
• Wikipedia: Trimethylsulfoxonium_iodide
• Wikidata: Q15427957
• ChEMBL ID: CHEMBL283149
• Mol file: 1774-47-6.mol

Synonyms:Trimethylsulfoxonium iodide;1774-47-6;Trimethylsulphoxonium iodide;Trimethyloxosulfonium iodide;Sulfoxonium, trimethyl-, iodide;Trimethyloxosulphonium iodide;Trimethyl sulphoxonium ioidie;MFCD00011899;Sulfoxonium, trimethyl-, iodide (1:1);S,S,S-Trimethylsulfoxonium iodide;Trimethylsulfoxoniumiodide;EINECS 217-204-2;NSC 71213;Sulfonium, trimethyl-, iodide, oxide;EC 217-204-2;C3H9IOS;Sulfoxonium, iodide;trimethysulfoxonium iodide;Sulfonium, iodide, oxide;trimehylsulphoxonium iodide;tri-methylsulfoxonium iodide;trimethyl sulfoxonium iodide;trimethyl-sulfoxonium iodide;C3H9OS.I;SCHEMBL2584;SCHEMBL2586;trimethyl sulphoxonium iodide;trimethyl-oxosulfonium iodide;trimethyloxo sulfonium iodide;Trimethyl-sulphoxonium iodide;trimethyl oxosulphonium iodide;tri-methyl-oxosulphonium iodide;Trimethyl-sulfoniumoxide iodide;S,S-Trimethylsulfoxonium iodide;C3-H9-O-S.I;Trimethyl(oxo)-sulfanylium iodide;DTXSID001014581;AMY24038;BCP13230;NSC71213;TriMethyl?sulfoxoniuM?iodide(TMSOI);AC7850;NSC-71213;trimethyl(oxo)-??-sulfanylium iodide;WLN: OS1&1&1 &Q &I;AKOS015833276;CS-W018549;Trimethyl(oxo)-gamma-sulfanylium iodide;AS-12135;SY002188;LS-148154;FT-0633832;T1065;J-200120;J-650228;Q15427957;F0001-0645

Chemical Property of Trimethylsulfoxonium iodide

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Melting Point: 208-212 °C (dec.)(lit.)
• PSA: 36.28000
• Density: 1.7074 (estimate)
• LogP: -2.62070
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive
• Solubility.: H2O: 50 mg/mL, clear
• Water Solubility.: 15 g/L (20 ºC)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 219.94188
• Heavy Atom Count: 6
• Complexity: 53

Purity/Quality:

99% ^*data from raw suppliers

Trimethylsulfoxonium iodide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C[S+](=O)(C)C.[I-]
• Uses: Treatment with strong base yields the ylide which adds to the carbonyl group of ketones1 and aldehydes2,3 to give epoxides. Also adds preferentially to the double bond of α,β-unsaturated esters to give cyclopropyl esters.4,5 Trimethylsulfoxonium Iodide is used to synthesize methylene-transfer reagents that are used in the preparation of epoxides. Trimethylsulfoxonium iodide is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride. The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides.

Technology Process of Trimethylsulfoxonium iodide

There total 6 articles about Trimethylsulfoxonium iodide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

dimethyl sulfoxide (67-68-5,8070-53-9) + methyl iodide (74-88-4) → trimethylsulfoxonium iodide (1774-47-6)

Guidance literature:

at 70 ℃; for 48h;

DOI:10.1055/s-0036-1588971

Reference yield: 28.0%

dimethyl sulfoxide (67-68-5,8070-53-9) → Na4(triiodide)3I(dimethylsulfoxide)15 + trimethylsulfoxonium iodide (1774-47-6)

Guidance literature:

dimethyl sulfoxide; With water; sodium hydroxide; at 20 ℃; for 0.5h; Ultrasonication;

With methyl iodide; at 20 ℃; for 144h; Ultrasonication;

DOI:10.1039/c1cc11898f

Reference yield:

acetic anhydride (108-24-7) + 3-O-(β-D-galactopyranosyl)-D-arabinose (61272-23-9,130767-77-0,130767-78-1) + methyl iodide (74-88-4) → Ethyl methyl sulfoxide (1669-98-3) + 1,3,4-tri-O-acetyl-2,5-di-O-methyl-D-arabinitol (100758-68-7) + 1,5-di-O-acetyl-2,3,4,6-tetra-O-methyl-D-galactitol (19285-93-9,19318-49-1,20316-14-7,25665-99-0,53403-07-9,81600-01-3,83290-15-7,103729-41-5,114183-58-3,25521-30-6) + 1,3,5-tri-O-acetyl-2,4-di-O-methyl-D-arabinitol (19318-22-0,19318-27-5,84885-38-1,84925-47-3,100758-67-6) + trimethylsulfoxonium iodide (1774-47-6)

Guidance literature:

With sodium tetrahydroborate; perchloric acid; trimethylsulfoxonium iodide; trifluoroacetic acid; In dimethyl sulfoxide; Product distribution; Improved methylation analysis; other saccharides;

DOI:10.1016/0008-6215(84)85106-X

upstream raw materials:

dimethyl sulfoxide

methyl iodide

acetic anhydride

3-O-(β-D-galactopyranosyl)-D-arabinose

Downstream raw materials:

6-(4-nitro-benzoyl)-1-oxa-6-aza-spiro[2.5]octane

Dimethyl-oxo-sulfonium-

rac-(16Ξ,20Ξ)-4-benzyl-16,17-epoxy-1-methyl-(15ξH)-19,20-dihydro-4,21-seco-sarpagane-21-nitrile

N-benzyl-1-oxa-6-azaspiro[2,5]-octane

Refernces

Catalytic asymmetric cyclopropanation of enones with dimethyloxosulfonium methylide promoted by a La-Li₃-(Biphenyldiolate)₃ + NaI complex

10.1021/ja076797c

The study presents a novel catalytic asymmetric cyclopropanation reaction of enones using dimethyloxosulfonium methylide, promoted by a La-Li3-(biphenyldiolate)3 + NaI complex. The reaction showcases high enantioselectivity, with up to 99% ee, and is applicable to a variety of enones, including those with electron-withdrawing or electron-donating substituents and heteroaryl-substituted enones. The use of NaI as an additive, along with biphenyldiol as a ligand, is crucial for achieving this level of selectivity. The reaction conditions were optimized to allow for slow addition of enones, which further improved the enantioselectivity. The study also explores the potential of the catalyst system with other substrates, such as an N-acylpyrrole, and discusses the role of NaI in the reaction mechanism, suggesting a partial alkali metal exchange occurs in situ to form a La-Li2-Na-(biphenyldiolate)3 complex. The findings provide a complementary approach to existing methods for catalytic asymmetric cyclopropanation and highlight the importance of the mixed-alkali metal system in achieving high yields and enantioselectivity.

Facile preparation of N-Tosyl-L-Phenylalanine chloromethyl ketone

10.2174/157017809790443005

The study presents a new method for preparing N-tosyl-L-phenylalanine chloromethyl ketone (TPCK), an irreversible serine protease inhibitor, without using toxic and explosive diazomethane. L-Phenylalanine is first tosylated to form N-tosyl-L-phenylalanine, which is then converted into its 4-nitrophenyl ester using DCC and DMAP. This ester reacts with dimethylsulfoxonium methylide, generated from trimethylsulfoxonium iodide and potassium tert-butoxide, to form a sulfur ylide. The sulfur ylide is subsequently treated with lithium chloride and methanesulfonic acid to produce the chloroketone, TPCK. This method achieves an overall yield of 36% and avoids the use of hazardous diazomethane, providing a safer and practical synthesis route.